LITTLE ROCK, Ark. (AP) — Arkansas has executed three inmates in the past week using a sedative that’s been the subject of multiple court challenges since it was first used by Florida in 2013. A look at midazolam and its role in U.S. executions:

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HOW DOCTORS USE IT

Midazolam is an anti-anxiety drug, similar to Valium or Ativan. It can be used to reduce anxiety before surgery and to sedate patients. Some states have used it in smaller doses to calm inmates before an execution under the brand name Versed.

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WHAT STATES ARE USING IT

Six states have used midazolam as the first step in either a two- or three-drug lethal injection: Alabama, Arizona, Florida, Ohio, Oklahoma and now Arkansas. States began using midazolam as an alternative after drugmakers began clamping down on the use of other products such as sodium thiopental or pentobarbital in lethal injections.

According to statistics from the Death Penalty Information Center, midazolam has been used in 23 of the 130 executions that have occurred since 2013, when Florida first used the drug to execute William Happ.

Arkansas’ supply of midazolam expires at the end of April. The state’s prison director has said Arkansas has no new supply of the drug readily available.

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HOW MIDAZOLAM HAS WORKED IN EXECUTIONS

In more than a dozen instances, midazolam executions have occurred with no apparent complications. But in a handful of lethal injections, clear problems emerged.

In Ohio, inmate Dennis McGuire repeatedly gasped and snorted over 26 minutes during his January 2014 lethal injection that used midazolam. Executions have been on hold in Ohio since then. About three months later in Oklahoma, inmate Clayton Lockett writhed and moaned on the gurney before state officials tried to halt the execution midway through it. He died anyway 43 minutes after the execution began, and an investigation later showed that his IV had been improperly placed in his groin.

And in Arizona in July 2014, Joseph Rudolph Wood gasped and snorted for more than 90 minutes after his execution began, prompting lawyers to file an emergency appeal with the U.S. Supreme Court demanding that it be stopped. Wood was pronounced dead one hour and 57 minutes after the execution started.

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WHAT COURTS HAVE SAID

The Lockett execution in Oklahoma prompted a review of midazolam by the U.S. Supreme Court, which upheld the protocol as constitutional in a 5-4 vote in June 2015.

Justice Samuel Alito said for a conservative majority that arguments the drug could not be used effectively in executions were speculative, and he dismissed problems in executions in Arizona and Oklahoma as “having little probative value for present purposes.”

In a dissent, Justice Sonia Sotomayor wrote, “Under the court’s new rule, it would not matter whether the state intended to use midazolam or instead to have petitioners drawn and quartered, slowly tortured to death or actually burned at the stake.”

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WHAT’S HAPPENING IN ARKANSAS

Arkansas has used midazolam in a far larger single dose than what was used in the problematic executions in Ohio, Oklahoma and Arizona.

Arkansas’ protocol calls for a 500-miligram megadose of midazolam. The execution policy used to put McGuire to death in Ohio called for 10 milligrams of midazolam. Lockett received 100 milligrams of the drug, while Wood received 15 doses of midazolam that were 50 milligrams each over the span of two hours.

On Monday night in Arkansas, attorneys suggested that Jack Jones’ execution “appeared to be torturous and inhumane” because Jones was moving his lips shortly after the drug was administered. Jones’ execution lasted 14 minutes, and state prison officials said Jones was talking to the prison director in the death chamber, not “gulping for air” as attorneys argued.

Arkansas plans to execute another inmate, Kenneth Williams, on Thursday night.

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Follow Jill Bleed on Twitter at www.twitter.com/jzbleed .

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